Study of <i>cis/trans</i> and <i>endo/exo</i> Diastereoselectivity in the [4+3]-Cycloaddition Reaction of 2-Functionalized Furans and Dimethyloxyallyl Cation: Preparation of Versatile Cycloheptane Synthons

• Angel M Montaña

  Departamento de Química Orgánica, Universidad de BarcelonaMartí i Franqués 1-11, 08028-Barcelona , Spain

• Sandra Ribes

  Departamento de Química Orgánica, Universidad de BarcelonaMartí i Franqués 1-11, 08028-Barcelona , Spain

• Pedro M Grima

  Departamento de Química Orgánica, Universidad de BarcelonaMartí i Franqués 1-11, 08028-Barcelona , Spain

• Francisca García

  Departamento de Química Orgánica, Universidad de BarcelonaMartí i Franqués 1-11, 08028-Barcelona , Spain

Abstract

A study on the influence of steric and electronic effects of a function attached at C-2 of furans in the yield and diastereoselectivity of [4+3] cycloaddition reactions with oxyallyl cations is presented. In almost all studied furans a cis diastereospecificity and a high endo diastereoselectivity is observed. Increasing bulkyness of the function attached at C-2 of furans, increases the endo diastereoselectivity, but decreases yield. Increasing the electronic density of the furan system, by an electron donating group attached at C-2, increases yield and diastereoselectivity.

Journal

• Chemistry Letters

  Chemistry Letters 26 (9), 847-848, 1997-09-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169062827648
• NII Article ID: 10002614510
• NII Book ID: AA00603318
• DOI: 10.1246/cl.1997.847
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/26/9/847/56074097/cl.1997.847.pdf
• Data Source:
  • Crossref
  • CiNii Articles